The Chicago Cubs have landed the biggest free agent of the offseason late last night by signing LHP Jon Lester to a 6-year $155 Million deal with a $30 million dollar signing bonus to be paid over the life of the contract. Also Jon Lester has a few vesting options that pertain to innings pitched towards the back end of the deal that could make it a 7-year contract. In addition Lester will be allotted 25 hours for use in a private jet paid for by the organization. Jon Lester was the first pick of the Boston Red Sox’s ownership of John Henry and Tom Werner in 2001 and yesterday he decided to spurn his old team for the opportunity to rewrite history again with the Chicago Cubs. GM Jed Hoyer and Theo Epstein did a fabulous job of putting this deal together and it all started with the signing of Joe Maddon to be their manager. Yes the contract will have a lot of bad money on the back end unless Lester performs until he’s 37. However that seems highly unlikely considering the innings he already has at age 31. Then again in the age of modern medicine anything is possible. The signing of Lester now gives the Cubs a bonafide ace to anchor their rotation for at least the next four years, while immediately putting them in the conversation to compete next year for at least a divisional crown. The Cubs since the signing of Maddon as the manager and now Lester have been moved to 12:1 to reverse their 107 years of losing.

Lester is a horse and with this signing allows for other pitchers to be bumped down into more suitable slots in the rotation. The Cubs rotation next year should go something like Lester, Wood, Arrietta, Jackson, and Hammel. Maddon may want to break up the two lefties during a series, also the back end is very much a coin flip depending on how either of the two are pitching coming out of spring training. The Cubs in addition to adding Lester for the $155 million added catcher Jesus Montero from the Diamondbacks for a battery mate. Obviously the Cubs have Wellington Castillo already and Kyle Schwarber on the way, but this is where Theo and Jed will try and work their magic some more in trying to move pieces around to garner more help in the bullpen or the outfield. The Cubs have a surplus of players, but a lot of their issues come in the form of where to play them continuously. A player like Alcantara is penciled in as a centerfielder, but has the ability to play all over the diamond with his versatility.

The idea of the Cubs now landing Cole Hamels seems a bit harder to fit in with the money they’ve just doled out to Montero and Lester. The Cubs are certainly not going to stop trying to improve this winter, but the fireworks may be over for now in terms of big name targets. The Cubs could try and piece something together for a more affordable pitcher like they’ve done so many times recently, but as of right now the Cubs have a very good starting rotation from top to bottom. The Cubs have a surplus of starters if you add in the likes of Kyle Hendricks and Tsuyoshi Wada. Kyle Hendricks pitched very well for the Cubs in 13 starts going 7-2 with a 2.46 ERA and could contend for a spot in the rotation with Edwin Jackson who needs to have a very strong March and April in order to not be jettisoned to the bullpen.

The surplus of starters could land them the bullpen help they desperately need. Wada would be the likely candidate to either be moved to the bullpen or flipped for some late inning relief. The presence of Castro with the emerging infield depth is another player that could be moved, however the deal would have to be a big return for Hoyer and Epstein to entertain the idea. Castro is coming off one of his better seasons as a pro and with the support expected around him, he should get a lot more pitches to hit if he’s able to stay on the field.

The Cubs and White Sox have made big splashes in the winter hot stove season. The Cubs can now start to look at themselves as no longer in the rebuilding mode anymore. Their time’s now and although they have a very young team, they have a very talented one that should be able to score a lot of runs. Kris Bryant should be the everyday third-baseman and Castro and Soler should be the double play combination. Add a healthy Rizzo and Montero to that mix, and you’re looking at one good looking infield. Soler in right with Alcantara in center and maybe Mike Olt in left and the Cubs will a tough out. There’s a still a lot of work to be done, but the Chicago baseball scene just got a whole lot more fun to watch this summer with the signing of a few marquee players on both sides of the river.